Though he's fully clothed, the portrait is revealing: Tullman is holding a 7-Eleven “Double Gulp” of Diet Coke.

“Sadly, I drink at least 100 ounces a day,” says the CEO of 1871, an organization that grooms digital startups in Chicago.

All that caffeine explains a lot.

Along with running the tech community headquartered at the Merchandise Mart, Tullman sits on a dozen nonprofit and civic boards, is working on a screenplay and is a serious art collector. On the weekends, he writes a blog about entrepreneurship.

He is leading 1871 at a time of enormous change. The tech hub is adding another floor to its Mart offices, it's working to attract big companies to connect with startups and it's making plans for tech incubators in new fields, including retail.

NO CONSENSUS

Tullman also is wrestling with how to increase women's participation in tech. A year after announcing plans for a women-centric incubator, funded in part by philanthropist Liz Lefkofsky, he says the organization couldn't find consensus on how to make it succeed. So he's working with 1871's board to spread funding more broadly to help women get access to training, technology and mentors. The organization says nearly a third of its 725 members are women.

Chicago Tribune columnist Melissa Harris called the move away from a women's incubator “utter neglect,” but others say it's impossible to squeeze all the needs of women techies into one vertical program.

Maura O'Hara, executive director of the Illinois Venture Capital Association and an 1871 board member, says it's not a “de minimis issue.” But as with any entrepreneurial venture, a new program takes a while to gel, she says.

“Howard excels at getting people really excited about initiatives. He puts a germ of an idea out there and people get excited and then there are energy and resources around it,” O'Hara says. “Howard needs to be allowed and the board needs to be allowed to start something and watch it evolve over time.”

Away from work, Tullman is fine-tuning a screenplay that started as a play and was featured byVictory Gardens Theater in 2011 as part of a fundraising effort for guest playwrights. He says he has a representative in Los Angeles but isn't seeking financing for the work yet.

STEALING MILLIONS

It's about five young friends who take low-level jobs in a presidential campaign and then steal millions without anyone noticing. “The candidate and senior management of a campaign are the least knowledgeable about any operational details of a campaign. There's enormous scrutiny on money coming in to a campaign and zero on how it's spent,” says Tullman, a regular donor to political campaigns.

Tullman, 69, who will be honored in May by the Illinois Humanities Council for his work in technology and the arts, started collecting Pez dispensers and lunchboxes when he was growing up and continued as an adult “enabled by eBay,” he says. When his two now-grown daughters were young, he bought Madame Alexander dolls, once traveling hundreds of miles to get one repaired.

Today, he and Judith, his wife of 30 years, collect art that they showcase in a private gallery. With more than 1,500 pieces and the time it takes to seek out new artists, it's like a business, he says.

So how did he have time to pose for Robbins' painting?

“She shot a million photos of me while I was working,” Tullman says. “I couldn't have sat still for that long.”